Oxime ethers and fungicides containing these compounds

ABSTRACT

Oxime ethers of the formula ##STR1## where R 1  and R 2  are hydrogen or alkyl, X(m=1 to 5) is halogen, cyano, trifluoromethyl, nitro, alkyl, alkoxy, unsubstituted or substituted phenyl, unsubstituted or substituted phenoxy, unsubstituted or substituted benzyloxy or hydrogen, and Y is methyleneoxy, oxymethylene, ethylene, ethynylene or oxygen, and fungicides containing these compounds.

This application is a continuation of application Ser. No. 069,224,filed on July 2, 1987, now abandoned.

The present invention relates to novel oxime ether derivatives, theirpreparation and their use as fungicides.

It is known that N-tridecyl-2,6-dimethylmorpholine and its salts, forexample the acetate, can be used as fungicides (DE-1 164 152 and 1 173722). However, their action is inadequate in some cases. It is alsoknown that acrylic acid derivatives, eg. methyl2-(4-[p-chlorostyryl]-phenyl)-3-methoxyacrylate, can be used asfungicides (European Pat. No. 178,826). However, their action isunsatisfactory.

We have found that novel oxime ether derivatives of the formula I##STR2## where R¹ and R² are identical or different and are eachhydrogen or alkyl of 1 to 5 carbon atoms, the radicals X (m=1 to 5) areidentical or different substituents from the group consisting ofhalogen, cyano, trifluoromethyl, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy,unsubstituted or substituted phenyl, unsubstituted or substitutedphenoxy, unsubstituted or substituted benzyloxy and hydrogen, and Y ismethyleneoxy, oxymethylene, ethylene, ethenylene, ethynylene or oxygen,not only possess very high fungitoxic activity but also are very welltolerated by plants.

Because of the C═N double bond, the novel compounds of the formula I areobtained in their preparation in the form of E/Z isomer mixtures, whichcan be separated into the individual components in a conventionalmanner, for example by crystallizaton or chromatography. The inventionrelates both to the individual isomeric compounds and to mixtures ofthese.

R¹ is preferably hydrogen or C₁ -C₃ -alkyl, such as methyl, ethyl orisopropyl, and R² is preferably hydrogen or C₁ -C₅ -alkyl, such asmethyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl,tert-butyl, n-pentyl or neopentyl.

X is preferably hydrogen, 2-fluoro, 3-fluoro, 4-fluoro,2-chloro-6-fluoro, 2-chloro, 3-chloro, 4-chloro, 2-bromo, 3-bromo,4-bromo, 2,4-dichloro, 2,6-dichloro, 3,5-dichloro, 2,4,6-trichloro,2-chloro-4-methyl, 2-methyl-4-chloro, 2-methyl, 3-methyl, 4-methyl,4-ethyl, 4-isopropyl, 4-tert-butyl, 2,4-dimethyl, 2,6-dimethyl,2,4,6-trimethyl, 2-methoxy-4-methyl, 4-methoxy-2-methyl, 2-methoxy,3-methoxy, 4-methoxy, 4-ethoxy, 4-isopropoxy, 2-trifluoromethyl,3-trifluoromethyl, 4-trifluoromethyl, 2-cyano, 4-cyano, 3-nitro,4-nitro, 4-phenyl, 4-benzyloxy, 4-phenoxy, halophenoxy,4-(2-chlorophenoxy), 4-(2,4-dichlorophenoxy), C₁ -C₄ -alkylphenoxy,4-(2-methylphenoxy), 3-benzyloxy, halobenzyloxy, 3-(2-chlorobenzyloxy),3-(2,4-dichlorobenzyloxy), 3-(2-fluorobenzyloxy), 3-(4-bromobenzyloxy),C₁ -C₄ -alkylbenzyloxy, 3-(2-methylbenzyloxy), 3 -phenoxy,3-(2-chlorophenoxy), 3-(2,4-dichlorophenoxy), 3-(2-fluorophenoxy),3-(4-bromophenoxy) or 3-(2-methylphenoxy), and Y is preferably a --CH₂O--, --OCH₂ --, --CH₂ --CH₂ --, --CH═CH-- or --C.tbd.C-- group or O.

The novel compounds can be prepared by reacting an α-ketocarboxylate ofthe formula II ##STR3## where X_(m), Y and R¹ have the above meanings,

(a) with an O-substituted hydroxylamine of the general formula III

    H.sub.2 N--O--R.sup.2                                      (III)

where R² has the above meanings, or

(b) with hydroxylamine to give the corresponding oxime, and thenreacting the product with a halogen derivative of the formula IV

    R.sup.2 --X                                                (IV)

where R² has the above meanings and X is halogen (F, Cl, Br or I), orwith a dialkyl sulfate.

The α-ketocarboxylates of the formula II can be prepared, for example,by reacting the corresponding aromatic Grignard compounds withimidazolides of the formula V ##STR4## where R¹ has the above meanings(J. S. Nimitz and H. S. Mosher, J. Org. Chem. 46 (1981), 211-213.

The Example which follows illustrates the preparation of the novelcompounds of the formula I.

(a) Preparation of methyl 2-(benzyloxy)-phenylglyoxylate

0.1 mole of a Grignard compound prepared from 1-benzyloxy-2-bromobenzeneand magnesium turnings in tetrahydrofuran is slowly added dropwise 14.6g (95 millimoles) of methyloxalylimidazole in tetrahydrofuran undernitrogen at -50° C. The mixture is allowed to come slowly to roomtemperature (20° C.) over a period of 4 hours. It is poured onto icewater and extracted several times with ether. The combined ether phasesare washed neutral and dried. After the solvent has been evaporated off,the product is brought to crystallization with n-pentane to give 16 g(62%) of colorless crystals of the abovementioned compound.

¹ H-NMR (CDCL₃): δ=3.35 (s, 3H), 5.07 (s, 2H), 7.05 (m, 2H), 7.40 (m,5H), 7.55 (m, 1H), 7.90 (m, 1H).

(b) Preparation of (Z)-(2-benzyloxyphenyl)-glyoxylic acid methyl esterO-methyloxime (compound no. 83)

15.5 g (57 millimoles) of methyl 2-(benzyloxy)-phenylglyoxylate in 160ml of methanol are initially taken, and 11.5 g of sodium carbonate and9.45 g (114 millimoles) of O-methylhydroxylamine hydrochloride areadded. The stirred mixture is refluxed for 24 hours. 100 ml of water areadded, after which the mixture is extracted several times with ethylacetate and the ethyl acetate solution is dried with Na₂ SO₄ and thenevaporated down.

11 g (65%) of the abovementioned compound are obtained in the form of anisomer mixture. Mixing with n-pentane gives the pure (Z)-isomer as whitecrystals of melting point 129°-132° C.

¹³ C-NMR (CDCL₃): δ=51.50, 62.92, 70.93, 112.60, 120.49, 121.33, 128.19,128.52 (2c) 129.04 (3C), 131.70, 135.92, 148.44, 156.50, 163.84.

The compounds listed in the Table below can be prepared by appropriatelymodifying the above data.

    __________________________________________________________________________     ##STR5##                                         (I)                         Comp.                                                                         No. X.sub.m       Y         R.sup.1                                                                           R.sup.2                                                                           Isomer                                                                            Mp(°C.)                                                                      IR(cm.sup.-1)                   __________________________________________________________________________    1   H             CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      2   2-F           CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      3   3-F           CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      4   4-F           CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      5   2-Cl, 6-F     CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      6   2-Cl          CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      7   3-Cl          CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      8   4-Cl          CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      9   2-Br          CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      10  3-Br          CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      11  4-Br          CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      12  2,4-Cl.sub.2  CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      13  2,6-Cl.sub.2  CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      14  3,5-Cl.sub.2  CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      15  2,4,6-Cl.sub.3                                                                              CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      16  2-Cl, 4-CH.sub.3                                                                            CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      17  2-CH.sub.3, 4-Cl                                                                            CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      18  2-CH.sub.3    CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      19  3-CH.sub.3    CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      20  4-CH.sub.3    CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      21  4-C.sub.2 H.sub.5                                                                           CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      22  4-i-C.sub.3 H.sub.7                                                                         CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      23  4-t-C.sub.4 H.sub.9                                                                         CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      24  2,4-(CH.sub.3).sub.2                                                                        CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      25  2,6-(CH.sub.3).sub.2                                                                        CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      26  2,4,6-(CH.sub.3).sub. 3                                                                     CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      27  2-OCH.sub.3, 4-CH.sub.3                                                                     CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      28  4-OCH.sub.3, 2-CH.sub.3                                                                     CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      29  2-OCH.sub.3   CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      30  3-OCH.sub.3   CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      31  4-OCH.sub.3   CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      32  4-OC.sub.2 H.sub.5                                                                          CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      33  4-Oi-C.sub.3 H.sub.7                                                                        CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      34  2-CF.sub.3    CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      35  3-CF.sub.3    CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      36  4-CF.sub.3    CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      37  2-CN          CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      38  4-CN          CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      39  3-NO.sub.2    CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      40  4-NO.sub.2    CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      41  4-C.sub.6 H.sub.5                                                                           CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      42  H             CHCH      CH.sub.3                                                                          CH.sub.3                                                                          Z   oil   2960, 1740,                                                                   1496, 1455,                                                                   1227, 1043,                                                                   1017, 962,                                                                    760, 692                        43  2-F           CHCH      CH.sub.3                                                                          CH.sub.3                                      44  3-F           CHCH      CH.sub.3                                                                          CH.sub.3                                      45  4-F           CHCH      CH.sub.3                                                                          CH.sub.3                                      46  2-Cl, 6-F     CHCH      CH.sub.3                                                                          CH.sub.3                                      47  2-Cl          CHCH      CH.sub.3                                                                          CH.sub.3                                      48  3-Cl          CHCH      CH.sub.3                                                                          CH.sub.3                                      49  4-Cl          CHCH      CH.sub.3                                                                          CH.sub.3                                                                          E/Z oil   2970, 1740,                                                                   1492, 1456,                                                                   1228, 1091,                                                                   1044, 1013,                                                                   962, 813                                                                      753                             50  2-Br          CHCH      CH.sub.3                                                                          CH.sub.3                                      51  3-Br          CH CH     CH.sub.3                                                                          CH.sub.3                                      52  4-Br          CHCH      CH.sub.3                                                                          CH.sub.3                                      53  2,4-Cl.sub.2  CHCH      CH.sub.3                                                                          CH.sub.3                                      54  2,6-Cl.sub.2  CHCH      CH.sub.3                                                                          CH.sub.3                                      55  3,5-Cl.sub.2  CHCH      CH.sub.3                                                                          CH.sub.3                                      56  2,4,6-Cl.sub.3                                                                              CHCH      CH.sub.3                                                                          CH.sub.3                                      57  2-Cl, 4-CH.sub.3                                                                            CHCH      CH.sub.3                                                                          CH.sub.3                                      58  2-CH.sub.3, 4-Cl                                                                            CHCH      CH.sub.3                                                                          CH.sub.3                                      59  2-CH.sub.3    CHCH      CH.sub.3                                                                          CH.sub.3                                      60  3-CH.sub.3    CHCH      CH.sub.3                                                                          CH.sub.3                                      61  4-CH.sub.3    CHCH      CH.sub.3                                                                          CH.sub.3                                      62  3-CH.sub.3    CHCH      CH.sub.3                                                                          CH.sub.3                                      63  4-i-C.sub.3 H.sub.7                                                                         CHCH      CH.sub.3                                                                          CH.sub.3                                      64  4-t-C.sub.4 H.sub.9                                                                         CHCH      CH.sub.3                                                                          CH.sub.3                                      65  2,4-(CH.sub.3).sub.2                                                                        CHCH      CH.sub.3                                                                          CH.sub.3                                      66  2,6-(CH.sub.3).sub.2                                                                        CHCH      CH.sub.3                                                                          CH.sub.3                                      67  2,4,6-(CH.sub.3).sub.3                                                                      CHCH      CH.sub.3                                                                          CH.sub.3                                      68  2-OCH.sub.3, 4-CH.sub.3                                                                     CHCH      CH.sub.3                                                                          CH.sub.3                                      69  4-OCH.sub.3, 2-CH.sub.3                                                                     CHCH      CH.sub.3                                                                          CH.sub.3                                      70  2-OCH.sub.3   CHCH      CH.sub.3                                                                          CH.sub.3                                      71  3-OCH.sub.3   CHCH      CH.sub.3                                                                          CH.sub.3                                      72  4-OCH.sub.3   CHCH      CH.sub.3                                                                          CH.sub.3                                      73  4-OC.sub.2 H.sub.5                                                                          CHCH      CH.sub.3                                                                          CH.sub.3                                      74  4-OiC.sub.3 H.sub.7                                                                         CHCH      CH.sub.3                                                                          CH.sub.3                                      75  2-CF.sub.3    CHCH      CH.sub.3                                                                          CH.sub.3                                      76  3-CF.sub.3    CHCH      CH.sub.3                                                                          CH.sub.3                                      77  4-CF.sub.3    CHCH      CH.sub.3                                                                          CH.sub.3                                      78  2-CN          CHCH      CH.sub.3                                                                          CH.sub.3                                      79  4-CN          CHCH      CH.sub.3                                                                          CH.sub.3                                      80  3-NO.sub.2    CHCH      CH.sub.3                                                                          CH.sub.3                                      81  4-NO.sub.2    CHCH      CH.sub.3                                                                          CH.sub.3                                      82  4-C.sub.6 H.sub.5                                                                           CHCH      CH.sub.3                                                                          CH.sub.3                                      83  H             CH.sub.2 O                                                                              CH.sub.3                                                                          CH.sub.3                                                                          Z   129-132                                                                             2940, 1737                                                                    1489, 1455                                                                    1343, 1278                                                                    1234, 1045                                                                    1027, 758                       84  2-F           CH.sub.2 O                                                                              CH.sub.3                                                                          CH.sub.3                                      85  3-F           CH.sub.2 O                                                                              CH.sub.3                                                                          CH.sub.3                                                                          E/Z 46-48 2970, 1734,                                                                   1592, 1492,                                                                   1452, 1278,                                                                   1231, 1028,                                                                   755                             86  4-F           CH.sub.2 O                                                                              CH.sub.3                                                                          CH.sub.3                                                                          E/Z 97-99 2970, 1740,                                                                   1600, 1513,                                                                   1487, 1276,                                                                   1224, 1042,                                                                   1025, 879,                                                                    751                             87  2-Cl, 6-F     CH.sub.2 O                                                                              CH.sub.3                                                                          CH.sub.3                                      88  2-Cl          CH.sub.2 O                                                                              CH.sub.3                                                                          CH.sub.3                                      89  3-Cl          CH.sub.2 O                                                                              CH.sub.3                                                                          CH.sub.3                                                                          E/Z oil   2970, 1742,                                                                   1600, 1490,                                                                   1453, 1279,                                                                   1228, 1044,                                                                   1024, 759                       90  4-Cl          CH.sub.2 O                                                                              CH.sub.3                                                                          CH.sub.3                                                                          Z   106-109                                                                             2975, 1738,                                                                   1598, 1489,                                                                   1277, 1235,                                                                   1041, 1026,                                                                   873, 759                        91  2-Br          CH.sub.2 O                                                                              CH.sub.3                                                                          CH.sub.3                                      92  3-Br          CH.sub.2 O                                                                              CH.sub.3                                                                          CH.sub.3                                      93  4-Br          CH.sub.2 O                                                                              CH.sub.3                                                                          CH.sub.3                                      94  2,4-Cl.sub.2  CH.sub.2 O                                                                              CH.sub.3                                                                          CH.sub.3                                      95  2,6-Cl.sub.2  CH.sub.2 O                                                                              CH.sub.3                                                                          CH.sub.3                                      96  3,5-Cl.sub.2  CH.sub.2 O                                                                              CH.sub.3                                                                          CH.sub.3                                      97  2,4,6-Cl.sub.3                                                                              CH.sub.2 O                                                                              CH.sub.3                                                                          CH.sub.3                                      98  2-CH.sub.3, 4-Cl                                                                            CH.sub.2 O                                                                              CH.sub.3                                                                          CH.sub.3                                      99  2-Cl, 4-CH.sub.3                                                                            CH.sub.2 O                                                                              CH.sub.3                                                                          CH.sub.3                                      100 2-CH.sub.3    CH.sub.2 O                                                                              CH.sub.3                                                                          CH.sub.3                                                                          E/Z       2970, 1735,                                                                   1489, 1454,                                                                   1278, 1231,                                                                   1045, 1025,                                                                   750                             101 3-CH.sub.3    CH.sub.2 O                                                                              CH.sub.3                                                                          CH.sub.3                                                                          E/Z 47-49 2970, 1736,                                                                   1600, 1490,                                                                   1453, 1279,                                                                   1227, 1045,                                                                   1026, 755                       102 4-CH.sub.3    CH.sub.2 O                                                                              CH.sub.3                                                                          CH.sub.3                                                                          E/Z 92-94 2970, 1736,                                                                   1600, 1490,                                                                   1454, 1278,                                                                   1232, 1043                                                                    1027, 761                       103 4-C.sub.2 H.sub.5                                                                           CH.sub.2 O                                                                              CH.sub.3                                                                          CH.sub.3                                      104 4-i-C.sub.3 H.sub.7                                                                         CH.sub.2 O                                                                              CH.sub.3                                                                          CH.sub.3                                      105 4-t-C.sub.4 H.sub.9                                                                         CH.sub.2 O                                                                              CH.sub.3                                                                          CH.sub.3                                      106 2,4-(CH.sub.3).sub.2                                                                        CH.sub.2 O                                                                              CH.sub.3                                                                          CH.sub.3                                      107 2,6-(CH.sub.3).sub.2                                                                        CH.sub.2 O                                                                              CH.sub.3                                                                          CH.sub.3                                      108 2,4,6-(CH.sub.3).sub.3                                                                       CH.sub.2 O                                                                             CH.sub.3                                                                          CH.sub.3                                      109 2-OCH.sub.3, 4-CH.sub.3                                                                     CH.sub.2 O                                                                              CH.sub.3                                                                          CH.sub.3                                      110 4-OCH.sub.3, 2-CH.sub.3                                                                     CH.sub.2 O                                                                              CH.sub.3                                                                          CH.sub.3                                      111 2-OCH.sub.3   CH.sub.2 O                                                                              CH.sub.3                                                                          CH.sub.3                                      112 3-OCH.sub.3   CH.sub.2 O                                                                              CH.sub.3                                                                          CH.sub.3                                      113 4-OCH.sub.3   CH.sub.2 O                                                                              CH.sub.3                                                                          CH.sub.3                                      114 4-OC.sub.2 H.sub.5                                                                          CH.sub.2 O                                                                              CH.sub.3                                                                          CH.sub.3                                      115 4-Oi-C.sub.3 H.sub.7                                                                        CH.sub.2 O                                                                              CH.sub.3                                                                          CH.sub.3                                      116 2-CF.sub.3    CH.sub.2 O                                                                              CH.sub.3                                                                          CH.sub.3                                      117 3-CF.sub.3    CH.sub.2 O                                                                              CH.sub.3                                                                          CH.sub.3                                      118 4-CF.sub.3    CH.sub.2 O                                                                              CH.sub.3                                                                          CH.sub.3                                      119 2-CN          CH.sub.2 O                                                                              CH.sub.3                                                                          CH.sub.3                                      120 4-CN          CH.sub.2 O                                                                              CH.sub.3                                                                          CH.sub.3                                      121 3-NO.sub.2    CH.sub.2 O                                                                              CH.sub.3                                                                          CH.sub.3                                      122 4-NO.sub.2    CH.sub.2 O                                                                              CH.sub.3                                                                          CH.sub.3                                      123 4-C.sub.6 H.sub.5                                                                           CH.sub.2 O                                                                              CH.sub.3                                                                          CH.sub.3                                      124 H             OCH.sub.2 CH.sub.3                                                                          CH.sub.3                                                                          E/Z oil   2940, 1742                                                                    1598, 1496                                                                    1239, 1227                                                                    1046, 1019                                                                    755                             125 2-F           OCH.sub.2 CH.sub.3                                                                          CH.sub.3                                      126 2-Cl          OCH.sub.2 CH.sub.3                                                                          CH.sub.3                                      127 4-Cl          OCH.sub.2 CH.sub.3                                                                          CH.sub.3                                      128 2,4-Cl.sub.2  OCH.sub.2 CH.sub.3                                                                          CH.sub.3                                      129 2-CH.sub.3, 4-Cl                                                                            OCH.sub.2 CH.sub.3                                                                          CH.sub.3                                      130 2-CH.sub.3    OCH.sub.2 CH.sub.3                                                                          CH.sub.3                                      131 4-CH.sub.3    OCH.sub.2 CH.sub.3                                                                          CH.sub.3                                      132 4-t-C.sub.4 H.sub.9                                                                         OCH.sub.2 CH.sub.3                                                                          CH.sub.3                                      133 2-OCH.sub.3   OCH.sub.2 CH.sub.3                                                                          CH.sub.3                                      134 2-CF.sub.3    OCH.sub.2 CH.sub.3                                                                          CH.sub.3                                      135 4-NO.sub.2    OCH.sub.2 CH.sub.3                                                                          CH.sub.3                                      136 H             ethynylene                                                                              CH.sub.3                                                                          CH.sub.3                                      137 2-F           ethynylene                                                                              CH.sub.3                                                                          CH.sub.3                                      138 2-Cl          ethynylene                                                                              CH.sub.3                                                                          CH.sub.3                                      139 2-Br          ethynylene                                                                              CH.sub.3                                                                          CH.sub.3                                      140 4-Br          ethynylene                                                                              CH.sub.3                                                                          CH.sub.3                                      141 2-CH.sub.3    ethynylene                                                                              CH.sub.3                                                                          CH.sub.3                                      142 4-CH.sub.3    ethynylene                                                                              CH.sub.3                                                                          CH.sub.3                                      143 2-OCH.sub.3   ethynylene                                                                              CH.sub.3                                                                          CH.sub.3                                      144 4-CF.sub.3    ethynylene                                                                              CH.sub.3                                                                          CH.sub.3                                      145 2-NO.sub.2    ethynylene                                                                              CH.sub.3                                                                          CH.sub.3                                      146 H             CHCH      CH.sub.3                                                                          H                                             147 H             CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          H                                             148 H             CHCH      CH.sub.3                                                                          C.sub.2 H.sub.5                               149 H             CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          C.sub.3 H.sub.7                               150 H             CHCH      CH.sub.3                                                                          C.sub.3 H.sub.7                               151 H             CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          i-C.sub.3 H.sub.7                             152 H             CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          t-C.sub.4 H.sub.9                             153 H             CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          C.sub.5 H.sub.11                              154 H             CHCH      C.sub.2 H.sub.5                                                                   CH.sub.3                                      155 H             CH.sub.2CH.sub.2                                                                        C.sub.2 H.sub.5                                                                   CH.sub.3                                      156 H             CHCH      i-C.sub.3 H.sub.7                                                                 CH.sub.3                                      157 H             CH.sub.2CH.sub.2                                                                        i-C.sub.3 H.sub.7                                                                 CH.sub.3                                      158 H             CHCH      C.sub.2 H.sub.5                                                                   C.sub.2 H.sub.5                               159 H             CH.sub.2CH.sub.2                                                                        C.sub.2 H.sub.5                                                                   C.sub.2 H.sub.5                               160 H             O         CH.sub.3                                                                          CH.sub.3                                      161 2-F           O         CH.sub.3                                                                          CH.sub.3                                      162 2-Cl          O         CH.sub.3                                                                          CH.sub.3                                      163 2-Br          O         CH.sub.3                                                                          CH.sub.3                                      164 4-Br          O         CH.sub.3                                                                          CH.sub.3                                      165 4-Cl          O         CH.sub.3                                                                          CH.sub.3                                      166 2-CH.sub.3    O         CH.sub.3                                                                          CH.sub.3                                      167 4-CH.sub.3    O         CH.sub.3                                                                          CH.sub.3                                      168 2-OCH.sub.3   O         CH.sub.3                                                                          CH.sub.3                                      169 4-OCH.sub.3   O         CH.sub.3                                                                          CH.sub.3                                      170 4-C.sub.6 H.sub.5                                                                           O         CH.sub.3                                                                          CH.sub.3                                      171 H             CHCH      H   H                                             172 H             CH.sub.2CH.sub.2                                                                        H   H                                             173 4-OCH.sub.2C.sub.6 H.sub.5                                                                  CHCH.sub.2                                                                              CH.sub.3                                                                          CH.sub.3                                      174 4-OCH.sub.2C.sub.6 H.sub.5                                                                  CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      175 4-OC.sub.6 H.sub.5                                                                          CHCH      CH.sub.3                                                                          CH.sub.3                                      176 4-OC.sub.6 H.sub.5                                                                          CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      177                                                                                ##STR6##     CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      178                                                                                ##STR7##     CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      179                                                                                ##STR8##     CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      180 3-OCH.sub.2C.sub.6 H.sub.5                                                                  CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      181                                                                                ##STR9##     CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      182                                                                                ##STR10##    CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      183                                                                                ##STR11##    CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      184                                                                                ##STR12##    CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      185                                                                                ##STR13##    CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      186 3-OC.sub.6 H.sub.5                                                                          CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      187                                                                                ##STR14##    CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      188                                                                                ##STR15##    CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      189                                                                                ##STR16##    CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      190                                                                                ##STR17##    CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      191                                                                                ##STR18##    CH.sub.2CH.sub.2                                                                        CH.sub.3                                                                          CH.sub.3                                      __________________________________________________________________________

In general terms, the novel compounds are extremely effective on a broadspectrum of phytopathogenic fungi, in particular those from the classconsisting of the Ascomycetes, Phycomycetes and Basidiomycetes. Some ofthem have a systemic action and can be used as foliar and soilfungicides.

The fungicidal compounds are of particular interest for controlling alarge number of fungi in various crops or their seeds, especially wheat,rye, barley, oats, rice, Indian corn, cotton, soybeans, coffee, sugarcane, fruit and ornamentals in horticulture and viticulture, and invegetables such as cucumbers, beans and cucurbits.

The novel compounds are particularly useful for controlling thefollowing plant diseases:

Erysiphe graminis in cereals,

Erysiphe cichoracearum and Sphaerotheca fuliginea in cucurbits,

Podosphaera leucotricha in apples,

Uncinula necator in vines,

Puccinia species in cereals,

Rhizoctonia solani in cotton,

Ustilago species in cereals and sugar cane,

Venturia inaequalis (scab) in apples,

Septoria nodorum in wheat,

Pyrenophora teres in barley,

Botrytis cinerea (gray mold) in strawberries and grapes,

Cercospora arachidicola in groundnuts,

Pseudocercosporella herpotrichoides in wheat and barley,

Pyricularia oryzae in rice,

Alternaria solani and Phytophthora infestans in potatoes and tomatoes,

Plasmopara viticola in grapes, and

Fusarium and Verticillium species in various plants.

The compounds are applied by spraying or dusting the plants with theactive ingredients, or treating the seeds of the plants with the activeingredients. They may be applied before or after infection of the plantsor seeds by the fungi.

The novel substances can be converted into conventional formulationssuch as solutions, emulsions, suspensions, dusts, powders, pastes andgranules. The application forms depend entirely on the purposes forwhich they are intended; they should at all events ensure a fine anduniform distribution of the active ingredient. The formulations areproduced in known manner, for example by extending the active ingredientwith solvents and/or carriers, with or without the use of emulsifiersand dispersants; if water is used as solvent, it is also possible toemploy other organic solvents as auxiliary solvents. Suitableauxiliaries for this purpose are solvents such as aromatics (e.g.,xylene, benzene), chlorinated aromatics (e.g., chlorobenzenes),paraffins (e.g., crude oil fractions), alcohols (e.g., methanol,butanol), amines (e.g., ethanolamine, dimethylformamide), and water;carriers such as ground natural minerals (e.g., kaolins, aluminas, talcand chalk) and ground synthetic minerals (e.g., highly disperse silicaand silicates); emulsifiers such as nonionic and anionic emulsifiers(e.g., polyoxyethylene fatty alcohol ethers, alkyl sulfonates and arylsulfonates); and dispersants such as lignin, sulfite waste liquors andmethylcellulose.

The fungicides generally contain from 0.1 to 95, and preferably from 0.5to 90, wt % of active ingredient.

The application rates are from 0.05 to 3 kg or more of active ingredientper hectare, depending on the type of effect desired. The novelcompounds may also be used for protecting materials, inter alia forcombating wood-destroying fungi such as Coniophora puteana andPolystictus versicolor. The novel active ingredients may also be used asfungicidal components of oily wood preservatives for protecting woodagainst wood-discoloring fungi. They are applied by treating, forexample impregnating or painting, the wood with them.

The agents and the ready-to-use formulations prepared from them, such assolutions, emulsions, suspensions, powders, dusts, pastes and granules,are applied in conventional manner, for example by spraying, atomizing,dusting, scattering, dressing or watering.

Examples of formulations are given below.

I. 90 parts by weight of compound no. 83 is mixed with 10 parts byweight of N-methyl-alpha-pyrrolidone. A mixture is obtained which issuitable for application in the form of very fine drops.

II. 20 parts by weight of compound no. 124 is dissolved in a mixtureconsisting of 80 parts by weight of xylene, 10 parts by weight of theadduct of 8 to 10 moles of ethylene oxide and 1 mole of oleicacid-N-monoethanolamide, 5 parts by weight of the calcium salt ofdodecylbenzene-sulfonic acid, and 5 parts by weight of the adduct of 40moles of ethylene oxide and 1 mole of castor oil. By pouring thesolution into water and uniformly distributing it therein, an aqueousdispersion is obtained.

III. 20 parts by weight of compound no. 83 is dissolved in a mixtureconsisting of 40 parts by weight of cyclohexanone, 30 parts by weight ofisobutanol, 20 parts by weight of the adduct of 7 moles of ethyleneoxide and 1 mole of isooctylphenol, and 10 parts by weight of the adductof 40 moles of ethylene oxide and 1 mole of castor oil. By pouring thesolution into water and finely distributing it therein, an aqueousdispersion is obtained.

IV. 20 parts by weight of compound no. 124 is dissolved in a mixtureconsisting of 25 parts by weight of cyclohexanol, 65 parts by weight ofa mineral oil fraction having a boiling point between 210° and 280° C.,and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1mole of castor oil. By pouring the solution into water and uniformlydistributing it therein, an aqueous dispersion is obtained.

V. 80 parts by weight of compound no. 83 is well mixed with 3 parts byweight of the sodium salt of diisobutylnaphthalene-alpha-sulfonic acid,10 parts by weight of the sodium salt of a lignin-sulfonic acid obtainedfrom a sulfite waste liquor, and 7 parts by weight of powdered silicagel, and triturated in a hammer mill. By uniformly distributing themixture in water, a spray liquor is obtained.

VI. 3 parts by weight of compound no. 124 is intimately mixed with 97parts by weight of particulate kaolin. A dust is obtained containing 3%by weight of the active ingredient.

VII. 30 parts by weight of compound no. 83 is intimately mixed with amixture consisting of 92 parts by weight of powdered silica gel and 8parts by weight of paraffin oil which has been sprayed onto the surfaceof this silica gel. A formulation of the active ingredient is obtainedhaving good adherence.

VIII. 40 parts by weight of compound no. 124 is intimately mixed with 10parts of the sodium salt of a phenolsulfonic acid-urea-formaldehydecondensate, 2 parts of silica gel and 48 parts of water to give a stableaqueous dispersion. Dilution in water gives an aqueous dispersion.

IX. 20 parts by weight of compound no. 83 is intimately mixed with 2parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8parts by weight of a fatty alcohol polyglycol ether, 2 parts by weightof the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensateand 68 parts by weight of a paraffinic mineral oil. A stable oilydispersion is obtained.

In these application forms, the agents according to the invention mayalso be present together with other active ingredients, for exampleherbicides, insecticides, growth regulators, and fungicides, and mayfurthermore be mixed and applied together with fertilizers. Admixturewith other fungicides frequently results in a greater fungicidal actionspectrum.

The following list of fungicides with which the novel compounds may becombined is intended to illustrate possible combinations but not toimpose any restrictions.

Examples of fungicides which may be combined with the novel compoundsare:

sulfur,

dithiocarbamates and their derivatives, such as

ferric dimethyldithiocarbamate,

zinc dimethyldithiocarbamate,

zinc ethylenebisdithiocarbamate,

manganese ethylenebisdithiocarbamate,

manganese zinc ethylenediaminebisdithiocarbamate,

tetramethylthiuram disulfides,

ammonia complex of zinc N,N'-ethylenebisdithiocarbamate,

ammonia complex of zinc N,N'-propylenebisdithiocarbamate,

zinc N,N'-propylenebisdithiocarbamate and

N,N'-polypropylenebis (thiocarbamyl) disulfide;

nitro derivatives, such as

dinitro(1-methylheptyl)-phenyl crotonate,

2-sec-butyl-4,6-dinitrophenyl 3,3-dimethylacrylate,

2-sec-butyl-4,6-dinitrophenyl isopropylcarbonate and

diisopropyl 5-nitroisophthalate;

heterocyclic substances, such as

2-heptadecylimidazol-2-yl acetate,

2,4-dichloro-6-(o-chloroanilino)-s-triazine,

O,O-diethyl phthalimidophosphonothioate,

5-amino-1-[-bis-(dimethylamino)-phosphinyl]-3-phenyl-1,2,4-triazole,

2,3-dicyano-1,4-dithiaanthraquinone,

2-thio-1,3-dithio[4,5-b]quinoxaline,

methyl 1-(butylcarbamyl)-2-benzimidazolecarbamate,

2-methoxycarbonylaminobenzimidazole,

2-(fur-2-yl)-benzimidazole,

2-(thiazol-4-yl)benzimidazole,

N-(1,1,2,2-tetrachloroethylthio)-tetrahydrophthalimide,

N-trichloromethylthiotetrahydrophthalimide,

N-trichloromethylthiophthalimide,

N-dichlorofluoromethylthio-N',N'-dimethyl-N-phenylsulfuric acid diamide,

5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole,

2-thiocyanatomethylthiobenzothiazole,

1,4-dichloro-2,5-dimethoxybenzene,

4-(2-chlorophenylhydrazono)-3-methyl-5-isoxazolone,

2-thiopyridine 1-oxide,

8-hydroxyquinoline and its copper salt,

2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiin,

2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiin 4,4-dioxide,

2-methyl-5,6-dihydro-5H-pyran-3-carboxanilide,

2-methylfuran-3-carboxanilide,

2,5-dimethylfuran-3-carboxanilide,

2,4,5-trimethylfuran-3-carboxanilide,

2,5-dimethyl-N-cyclohexylfuran-3-carboxamide,

N-cyclohexyl-N-methoxy-2,5-diethylfuran-3-carboxamide,

2-methylbenzanilide,

2-iodobenzanilide,

N-formyl-N-morpholine-2,2,2-trichloroethylacetal,

piperazine-1,4-diylbis-(1-(2,2,2-trichloroethyl)-formamide),

1-(3,4-dichloroanilino)-1-formylamino-2,2,2-trichloroethane,

2,6-dimethyl-N-tridecylmorpholine and its salts,

2,6-dimethyl-N-cyclododecylmorpholine and its salts,

N-[3-(p-tert.-butylphenyl)-2-methylpropyl]-cis-2,6-dimethylmorpholine,

N-[3-(p-tert.-butylphenyl)-2-methylpropyl]-piperidine,

1-[2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-ylethyl]-1H-1,2,4-triazole

1-[2-(2,4-dichlorophenyl)-4-n-propyl-1,3-dioxolan-2-ylethyl]-1H-1,2,4-triazole,

N-(n-propyl)-N-(2,4,6-trichlorophenoxyethyl)-N'-imidazolyl-urea,

1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-butan-2-one,

1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-butan-2-ol,

α-(2-chlorophenyl)-α-(4-chlorophenyl)-5-pyrimidinemethanol,

5-butyl-(2-dimethylamino-4-hydroxy-6-methylpyrimidine,

bis-(p-chlorophenyl)-3-pyridinemethanol,

1,2-bis-(3-ethoxycarbonyl-2-thioureido)-benzene,

1,2-bis-(3-methoxycarbonyl-2-thioureido)-benzene,

and various fungicides, such as

dodecylguanidine acetate,

3-[3-(3,5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyl]-glutaramide,

hexachlorobenzene,

DL-methyl-N-(2,6-dimethylphenyl)-N-fur-2-yl alanate,

methyl DL-N-(2,6-dimethylphenyl)-N-(2'-methoxyacetyl)-alanate,

N-(2,6-dimethylphenyl)-N-chloroacetyl-DL-2-aminobutyrolactone,

methyl DL-N-(2,6-dimethylphenyl)-N-(phenylacetyl)-alanate,

5-methyl-5-vinyl-3-(3,5-dichlorophenyl)-2,4-dioxo-1,3-oxazolidine,

3[3,5-dichlorophenyl]-5-methyl-5-methoxymethyl-1,3-oxazolidine-2,4-dione,

3-(3,5-dichlorophenyl)-1-isopropylcarbamylhydantoin,

N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide,

2-cyano-[N-(ethylaminocarbonyl)-2-methoximino]-acetamide,

1-[2-(2,4-dichlorophenyl)-pentyl]-1H-1,2,4-triazole,

2,4-difluoro-α-(1H-1,2,4-triazol-1-ylmethyl)-benzhydryl alcohol,

N-(3-chloro-2,6-dinitro-4-trifluoromethylphenyl)-5-trifluoromethyl-3-chloro-2-aminopyridine,and

1-((bis-(4-fluorophenyl)-methylsilyl)-methyl)-1H-1,2,4-triazole.

For the following experiments, the prior art active ingredientsN-tridecyl-2,6-dimethylmorpholine (A), its acetate (B) and methyl2-(4-[p-chlorostyryl]phenyl)-3-methoxyacrylate (C) were used forcomparison purposes.

USE EXAMPLE 1 Action on wheat mildew

Leaves of pot-grown wheat seedlings of the "Fruhgold" variety weresprayed with aqueous liquors containing (dry basis) 80% of activeingredient and 20% of emulsifier, and sprayed, 24 hours after thesprayed-on layer had dried, with spores of wheat mildew (Erysiphegraminis var. tritici). The plants were then set up in the greenhouse at20° to 22° C. and a relative humidity of 75 to 80%. The extent of mildewspread was assessed after 7 days.

The results of this experiment show that active ingredients nos. 42, 49,83, 100 and 124, applied as 0.025 and 0.006% (wt %) spray liquors, had abetter fungicidal action (90%) than prior art active ingredients A, Band C (70%).

USE EXAMPLE 2 Action on Plasmopara viticola

Leaves of potted vines of the Muller-Thurgau variety were sprayed withaqueous suspensions containing (dry basis) 80% of active ingredient and20% of emulsifier. To assess the duration of action, the plants were setup, after the sprayed-on layer had dried, for 8 days in the greenhouse.Then the leaves were infected with a zoospore suspension of Plasmoparaviticola. The plants were first placed for 16 hours in a watervapor-saturated chamber at 24° C. and then in a greenhouse for 5 days atfrom 20° to 30° C. To accelerate and intensify the sporangiophoredischarge, the plants were then again placed in the moist chamber for 16hours. The extent of fungus attack was then assessed on the undersidesof the leaves.

The results obtained in this experiment show that active ingredientsnos. 42, 49, 83, 89, 100 and 124, applied as 0.05% spray liquors, had agood fungicidal action (90%).

USE EXAMPLE 3 Action on Septoria nodorum

Leaves of pot-grown wheat seedlings of the "Jubilar" variety weresprayed to runoff with aqueous liquors containing (dry basis) 80% ofactive ingredient and 20% of emulsifier. On the following day the plantswere infected with an aqueous spore suspension of Septoria nodorum andfurther cultivated for 7 days at 17°to 19° C. and a relative humidity of95%. The extent of fungus spread was then assessed visually.

The results obtained show that active ingredients nos. 49, 83 and 124,applied as 0.05% spray liquors, had a good fungicidal action (90%).

We claim:
 1. An oxime ether of the formula I ##STR19## where R¹ is hydrogen or alkyl of 1 to 5 carbon atoms, R² is methyl, the radicals X (m=1 to 5) are identical or different substituents from the group consisting of halogen, cyano, trifluoromethyl, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, phenyl, unsubstituted or halo or alkyl substituted phenoxy, unsubstituted or halo or alkyl substituted benzyloxy, and hydrogen, and Y is methyleneoxy, oxymethylene, ethylene, ethenylene, ethynylene or oxygen.
 2. An oxime ether of the formula I as set forth in claim 1, where X is hydrogen, 2-fluoro, 3-fluoro, 4-fluoro, 2-chloro-6-fluoro, 2-chloro, 3-chloro, 4-chloro, 2-bromo, 3-bromo, 4-bromo, 2,4-dichloro, 2,6-dichloro, 3,5-dichloro, 2,4,6-trichloro, 2-chloro-4-methyl, 2-methyl-4-chloro, 2-methyl, 3-methyl, 4-methyl, 4-ethyl, 4-isopropyl, 4-tert.-butyl, 2,4-dimethyl, 2,6-dimethyl, 2,4,6-trimethyl, 2-methoxy-4-methyl, 4-methoxy-2-methyl, 2-methoxy, 3-methoxy, 4-methoxy, 4-ethoxy, 4-isopropoxy, 2-trifluoromethyl, 3-trifluoromethyl, 4-trifluoromethyl, 2-cyano, 4-cyano, 3-nitro, 4-nitro, 4-phenyl, 4-benzyloxy, 4-phenoxy, halophenoxy, 4-(2-chloro)-phenoxy, 4-(2,4-dichloro)-phenoxy, C₁ -C₄ -alkylphenoxy, 4-(2-methyl)-phenoxy, 3-benzyloxy, halobenzyloxy, 3-(2-chloro)-benzyloxy, 3-(2,4-dichloro)-benzyloxy, 3-(2-fluoro)-benzyloxy, 3-(4-bromo)-benzyloxy-, C₁ -C₄ -alkylbenzyloxy, 3-(2-methyl)-benzyloxy, 3-phenoxy, 3-(2-chloro)-phenoxy, 3-(2,4-dichloro)-phenoxy, 3-(2-fluoro)-phenoxy, 3-(4-bromo)-phenoxy or 3-(2-methyl)-phenoxy, R¹ is hydrogen, methyl, ethyl or isopropyl.
 3. A fungicidal agent containing an oxime ether of the formula I ##STR20## where R¹ is hydrogen or alkyl of 1 to 5 carbon atoms, R² is methyl, the radicals X (m=1 to 5) are identical or different substituents from the group consisting of halogen, cyano, trifluoromethyl, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, phenyl, unsubstituted or halo or alkyl substituted phenoxy, unsubstituted or halo or alkyl substituted benzyloxy, and hydrogen, and Y is methyleneoxy, oxymethylene, ethylene, ethenylene, ethynylene or oxygen, and inert carriers.
 4. A process for combating fungi, wherein an oxime ether of the formula I ##STR21## where R¹ and R² are identical or different and are each hydrogen or alkyl of 1 to 5 carbon atoms, the radicals X (m=1 to 5) are identical or different substituents from the group consisting of halogen, cyano, trifluoromethyl, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, phenyl, unsubstituted or halo or alkyl substituted phenoxy, unsubstituted or halo or alkyl substituted benzyloxy, and hydrogen, and Y is methyleneoxy, oxymethylene, ethylene, ethenylene, ethynylene or oxygen, is allowed to act on the fungi, or the areas, plants, materials or seed threatened by fungus attack.
 5. 2-Benzyloxyphenyl-glyoxylic acid methyl ester O-methyloxime.
 6. 2-Phenyloxymethylenephenyl-glyoxylic acid methyl ester O-methyloxime.
 7. The oxime ether according to claim 1, wherein Y is methyleneoxy.
 8. The oxime ether according to claim 1, wherein Y is oxymethylene.
 9. The oxime ether according to claim 1, wherein Y is ethylene.
 10. The oxime ether according to claim 1, wherein Y is ethenylene.
 11. The oxime ether according to claim 1, wherein Y is ethynylene.
 12. The oxime ether according to claim 1, wherein Y is oxygen.
 13. The oxime ether according to claim 2, wherein Y is --CH₂ O--.
 14. The oxime ether according to claim 2, wherein Y is --OCH₂ --.
 15. The oxime ether according to claim 2, wherein Y is --CH₂ CH₂ --.
 16. The oxime ether according to claim 2, wherein Y is --CH═CH--.
 17. The oxime ether according to claim 2, wherein Y is --C═C--.
 18. The oxime ether according to claim 2, wherein Y is --O--.
 19. The fungicidal agent of claim 3, wherein in the oxime ether Y is methyleneoxy.
 20. The fungicidal agent of claim 3, wherein in the oxime ether Y is oxymethylene.
 21. The fungicidal agent of claim 3, wherein in the oxime ether Y is ethylene.
 22. The fungicidal agent of claim 3, wherein in the oxime ether Y is ethenylene.
 23. The fungicidal agent of claim 3, wherein in the oxime ether Y is ethynylene.
 24. The fungicidal agent of claim 3, wherein in the oxime ether Y is oxygen.
 25. The process according to claim 4, wherein in the oxime ether Y is methyleneoxy.
 26. The process according to claim 4, wherein in the oxime ether Y is oxymethylene.
 27. The process according to claim 4, wherein in the oxime ether Y is ethylene.
 28. The process according to claim 4, wherein in the oxime ether Y is ethenylene.
 29. The process according to claim 4, wherein in the oxime ether Y is ethynylene.
 30. The process according to claim 4, wherein in the oxime ether Y is oxygen. 